Plot

The film centers on a group of aimless young men from a wealthy Texas community. As the movie opens, Dignan (Owen Wilson) "rescues" Anthony (Luke Wilson) from a voluntary mental hospital where he has been staying for self-described exhaustion. Dignan has an elaborate escape planned and has developed a 75-year plan, which he shows to Anthony on the escape bus. The plan is to pull off several heists and then meet up with Mr. Henry, a landscapist and part-time criminal known to Dignan.

The two friends waste no time in breaking into and robbing a house as a practice run, taking small, specific items from a list. During Dignan's critique of the robbery, he mentions that he took diamond earrings, which were not on the list. Anthony becomes angered because the house was his family's and he admonishes Dignan for stealing his mother's earrings without permission.

Anthony visits his little sister at her school so she can return the earrings. Dignan recruits Bob Mapplethorpe as a getaway driver because he is the only person they know with his own car. The three make a road trip to buy guns and return to Bob's house to plan their next heist, a local bookstore. The group bickers as Dignan struggles to describe his intricate plan to the others.

The group manages to steal a small sum of money from the bookstore and then "go on the lam" at a hotel on the side of the highway. At the hotel, Anthony meets Inés (Lumi Cavazos), a maid, and the two spark a romance despite Inés's lack of English. Meanwhile, Bob finds out that his marijuana crop has been discovered by police and consequently, his older brother has been arrested. Though Dignan and Anthony convince him to stay the night, by morning Bob has taken his car and left to help his brother.

Before leaving, Anthony gives Dignan an envelope for Inés. Dignan delivers the envelope to Ines while she is cleaning a room, without knowing the envelope has most of his and Anthony's money inside. Inés does not open the envelope and hugs Dignan to say goodbye. As Dignan is leaving, Inés runs to a friend of hers, who is nearby cleaning another room. This friend speaks good English and Ines asks him to chase after Dignan and tell him that she loves Anthony. Her friend is a boy, and when he chases after Dignan and delivers the message he says, "Tell Anthony I love him". Dignan misunderstands the friend and assumes he is speaking for himself and not Inés. And so, the message is never delivered to Anthony and Dignan is left feeling very confused.

Taking an abandoned Alfa Romeo Spider, Dignan and Anthony continue with the 75-year plan, but the car quickly breaks down. On the side of the road, Anthony reveals that the envelope Dignan gave to Inés contained the rest of their cash. The two get in a fight and they go their separate ways.

Narrating a letter to his sister, Anthony says he and Bob have settled down into a routine that's been keeping them busy. Dignan, who has subsequently joined Mr. Henry's gang, tracks Anthony down with fellow gang member Applejack and approaches him in an alley while Anthony is taking Bob's dog for a run. Dignan gives a somewhat hesitant apology and the two friends reconcile. Dignan invites Anthony into a job with Mr. Henry and Anthony accepts in the condition that Bob is allowed in as well.

The trio meet the eccentric Mr. Henry (James Caan) and begin to plan a heist to rob a safe at a nearby cold storage facility. Mr. Henry places himself as a role model for the trio, standing up to Bob's abusive brother and tutoring Dignan on success. He invites the trio to a party at his house and visits the group at the Mapplethorpe's house, which he compliments. Meanwhile, Anthony learns of Inés's love for him and he contacts her. She has learned some English and the two rekindle their relationship.

With two accomplices from Mr. Henry's landscaping company, the group attempts to conduct their heist at the factory, but the plan quickly falls apart. As the police arrive at the scene, Dignan has locked himself out of the escape van and is arrested. During the robbery, a cut-away reveals Mr. Henry loading furniture from Bob's house into a truck.

Anthony and Bob visit Dignan in prison. They catch up and tell him how Mr. Henry robbed Bob's house. Dignan begins rattling off an escape plan and instructs his friends to get into position for a get-away. After a tense moment, the two realize that Dignan is joking. Before leaving, Dignan says to Anthony, "Isn't it funny that you used to be in the nuthouse and now I'm in jail?" as he walks back into the prison. As in most Wes Anderson movies the ending is in slow motion.